1-Aroyl-5-oxo-2-pyrrolidinepropanoic acids and related esters

Abstract

1-Aroyl-5-oxo-2-pyrrolidinepropanoic acids, salts, and esters which are useful as pharmacological agents, especially as agents for the reversal of amnesia, enhancing performance in poorly motivated subjects and treatment of senility and methods for their preparations are disclosed. Pharmaceutical compositions containing said compounds, salts, and esters and methods for using said compositions in treating senility, improving motivation and reversal of amnesia are also taught.

I claim: 
     
       1. A compound of the formula ##STR17## wherein R is hydrogen and the pharmaceutically acceptable metal or amine salts thereof, alkyl or ##STR18## where Z is hydrogen alkyl, fluoro, chloro, bromo, or trifluoromethyl; X and Y are hydrogen, chloro, fluoro, hydroxy, amino, alkylamino, dialkylamino, methyl, alkoxy having from one to six carbon atoms or benzyloxy; wherein X and Y may be the same or different with the proviso that when R is hydrogen, or a pharmaceutically acceptable metal or amine cation, X is a substituent other then hydrogen. 
     
     
       2. The compounds of claim 1 wherein R is hydrogen, methyl, ethyl, benzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 4-trifluoromethylbenzyl, 4-methylbenzyl, sodium, potassium, calcium, ammonium, trimethylammonium or triethylammonium; X is 2-fluoro, 4-chloro, 4-fluoro, 2-methoxy, 3-methoxy, 3-methyl, Y-methoxy and Y is hydrogen; X is 3-benzyloxy or 3-hydroxy, 3-methyl and Y is 4-methoxy. 
     
     
       3. The compounds of claim 1 wherein R is hydrogen, sodium, potassium, calcium, magnesium or ammonium; X is 4-fluoro, 4-methoxy or 4-chloro and Y is hydrogen. 
     
     
       4. The compound of claim 1 having the name 1-(4-Methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid and pharmaceutically acceptable metal or amine salts. 
     
     
       5. The compound of claim 1 having the name 1-(3-Methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid and pharmaceutically acceptable metal or amine salts. 
     
     
       6. The compound of claim 1 having the name 1-(2-Methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid and pharmaceutically acceptable metal or amine salts. 
     
     
       7. The compound of claim 1 having the name 1-(3-Hydroxy-4-methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid and pharmaceutically acceptable metal or amine salts. 
     
     
       8. The compound of claim 1 having the name 1-(4-Fluorobenzoyl)-5-oxo-2-pyrrolidinepropanoic acid and pharmaceutically acceptable metal or amine salts. 
     
     
       9. The compound of claim 1 having the name 1-(2-Fluorobenzoyl)-5-oxo-2-pyrrolidinepropanoic acid and pharmaceutically acceptable metal or amine salts. 
     
     
       10. The compound of claim 1 having the name 1-(4-Chlorobenzoyl)-5-oxo-2-pyrrolidinepropanoic acid and pharmaceutically acceptable metal or amine salts. 
     
     
       11. The compound of claim 1 having the name 1-(2-Chlorobenzoyl)-5-oxo-2-pyrrolidinepropanoic acid and pharmaceutically acceptable metal or amine salts. 
     
     
       12. The compound of claim 1 having the name 1-(4-Methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester. 
     
     
       13. The compound of claim 1 having the name 1-(3-Methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester. 
     
     
       14. The compound of claim 1 having the name 1-(2-Methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester. 
     
     
       15. The compound of claim 1 having the name 1-(3-Hydroxy-4-methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester. 
     
     
       16. The compound of claim 1 having the name 1-(4-Fluorobenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester. 
     
     
       17. The compound of claim 1 having the name 1-(2-Fluorobenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester. 
     
     
       18. The compound of claim 1 having the name 1-(4-Chlorobenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester. 
     
     
       19. The compound of claim 1 having the name 1-(2-Chlorobenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester. 
     
     
       20. The compound of claim 1 having the name 1-(4-methoxy-3-methylbenzoyl)-5-oxo-2-pyrrolidinepropanoic acid and pharmaceutically acceptable metal or amine salts.